Real Estate Investing in Winston, Oregon

Everything the listing leaves out — vacancy, rent trend, cap rate, landlord climate. All free.

2 ZIP codes • Population: 7,871 • Douglas County

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Should you buy in Winston, OR? Our answer, based on the numbers below.

🏠 For Homebuyers
MIXED
Grade C (63/100)

Mixed signals — some positives, some negatives. Worth considering but not a slam-dunk.

📈 For Investors
MIXED
3.0 / 5 (47/100)

A middle-of-the-road market. Workable, but the best opportunities may be nearby ZIPs rather than this one.

⚠️ Risks to Know
CLEAN

No major risk flags on the data we track.

What’s happening in Winston, OR?

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3.0/ 5

Investability

Citywide average

3.0/ 5

Appreciation

5.0% 5yr CAGR

4.0/ 5

Landlord Climate

Regulatory friendliness

🏦 30-yr Fixed Rate: 6.76% as of Sep 10 Source: Freddie Mac PMMS
Avg Investability
Avg Home Value $273,356
Avg Monthly Rent $1,143
ZIP Codes 2

Investing in Winston Real Estate

This is a distressed-leaning corner of Oregon: Winston has 2 ZIPs and a sizable population, and the investment math only works for investors who truly understand the market.

Winston is the kind of market where the cap rate on paper and the cap rate realized tend to diverge. plainly out-of-state investors should be especially careful with the assumptions they carry in.

clearly Winston's sale market has not rewarded patience. better suited elsewhere for listings sit longer, price cuts are common, and rent growth has been flat to negative in multiple ZIPs.

A an established population with $N/AK household income profile is what makes Winston a challenging rental market — the tenant base is present, but the affordability math is tight.

A great house in the wrong ZIP is still a bad deal — screen every market by cash flow & cap rate.
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Best ZIP codes in Roseburg, OR

Winston is part of this metro. Every ZIP in it, ranked. Free.

Cash Flow → Appreciation → Affordable →

Landlord Ground Truth

Real numbers from people who own or manage rentals in Winston, OR. Anonymous, moderated, never written by AI.

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Avg Home Value
$273,356
Avg Monthly Rent
$1,143
1% Rule
✗ Below
Landlord Friendly (OR)

📉 Market Crash Risk Index

Based on Roseburg, OR metro

1/10
Low Risk
Price YoY
0/3
N/A
Rent YoY
0/2
N/A
Below List
1/3
54%
Days Pending
0/2
0 days

View all metro crash risk rankings →

☀️ Warm Market — Roseburg, OR metro
0
Days to pending
8.4%
Listings with price cuts
0.0%
Sale-to-list ratio
📅 Data as of August 29, 2026 — updated weekly

ZIP Codes in Winston, OR

Screen every ZIP in Winston

Filter Winston’s ZIPs by cap rate, vacancy, appreciation and 30+ more criteria, and export your shortlist to CSV — with the Investor plan ($19/mo).

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Frequently Asked Questions About Winston, OR

Is housing expensive in Winston, OR?

Winston, OR median home values land near $273K. That is reasonable territory for investors looking at $1,143/mo-per-month rentals.

What is the typical renter like in Winston, OR?

Winston, OR offers a stable renter base at the $1,143/mo rent level. Tenant turnover is reasonable for well-managed properties.

What is the typical vacancy rate in Winston, OR?

Winston, OR vacancy trends elevated. Investors running standard buy-and-hold plays see reasonable downtime between tenants.

How strict are landlord regulations in Winston, OR?

Rental owners in Winston, OR deal with a landlord-friendly legal framework. Most standard eviction processes run on reasonable timelines.

Is Winston in OR worth investing in?

Investors tracking Winston, OR will find a 3.0/5 rating supported by $273K median home values and $1,143/mo rents. That profile suits long-term holders targeting reliable returns.

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